Under the Tuscan Sun: An Intimate Wedding at Castello di Casole

It was love at first sight when Meg Scanlon, now a women’s apparel buyer at Ralph Lauren, spotted investment banker Michael McGillen from across the library way back in high school, but it took the introduction of Facebook onto the social scene for sparks to fly in real life. “We grew up in different suburbs outside of Chicago and both attended the same private Catholic prep school,” says Meg. “One morning, I noticed Michael. He was a year ahead of me so I didn’t know him at the time, but I instantly knew I had to meet him. When Facebook launched for high school students, we each happened to be two of the initial people from our school to join. I took it as a sign and boldly used it as a platform to introduce myself—which was very unusual for my shy high school self.” They started dating shortly thereafter and continued seeing each other while he was at Georgetown and she was at FIT.

After dating for almost 10 years, the two got engaged. “Since we met at such a young age, most of our relationship had been long distance,” explains Meg. “I was living in New York to pursue my career in fashion while Michael was working and going to business school in Chicago. We took a break for about a year and a half while we were both living in different cities, but we still talked constantly so it was never a question of if we would get back together, but when. I knew he was the one for me from the beginning.”

When the two officially began dating again, they made an effort to visit each other at least once a month. It was during one of Meg’s routine trips to Chicago when Michael proposed. “We usually stayed at my parent’s house so I could spend time with them as well,” explains Meg. “But mainly it was because I couldn’t handle Michael’s ‘dorm room’ apartment! The weekend of the proposal, my mom made a morning blowout appointment for me in town—I’m a total addict! The drive to the hair salon was a bit emotional because I knew I had a special day in store. When I got back to the house, Michael was standing in the driveway with the car packed and ready to go. We had a beautiful lunch at Nomi overlooking the Chicago lakefront, walked around the city, had a drink at RL, and checked-in to Soho House Chicago for the night. We toasted in the room with Champagne and then took a glass up to the roof. Once we were back in the room, drinking and listening to music, Michael gave me a book he had created filled with photos and captions from all our years together. The first page of the book had a picture from when he asked me to prom—he had drawn with paint on his parents’ car, ‘Will you go to prom with me?’ The pages following included high school and college memories, trips we had taken together, and time spent between New York, Washington, D.C., and Chicago. The last page of the book had the exact same picture from prom, but the words on the car now said ‘Will you marry me?’ His brother, who had the car in Boston, was a great sport and re-created the scene for Michael. I laughed, cried, and obviously said yes!” They spent the next hour calling family and friends to share their big news before heading off to dinner. “We arrived at Spiaggia to the staff congratulating us and then had the most amazing Italian dishes for dinner,” says Meg. “Afterward, we walked over to the Pump Room for drinks and all of our family and friends were waiting inside. We ended up celebrating and dancing all night long. Ordering room service in bed later that night really was the icing on the cake!”

Initially, Meg was very wary of a destination wedding. “Both of our families and the majority of our friends live in Chicago, and I didn’t want to inconvenience anyone by having our wedding so far away,” she says. “But, my mother had taken us to Castello di Casole two summers prior most likely to plant the seeds for a future Italian wedding. It was by far the most magical place I had ever been, and my entire family fell in love with the property and all of Tuscany. I’ve learned over the years that my mother is always right, and this was no exception.”

The couple knew they wanted an intimate wedding so they could spend as much time with their guests as possible and the idea of having an entire weekend celebration, as opposed to just one night, appealed to them—so ultimately a destination wedding was the right fit. Meg and Michael worked with wedding planner Silvia Galli from SposiamoVi—“I couldn’t have done it without her! We quickly realized how important it is to have a local wedding planner when you’re getting married abroad.”

The weekend kicked off with a day at Avignonesi Vineyard in Montepulciano. Guests did tours of the cellars and vineyards, had lunch on the terrace, and of course, drank lots of Tuscan wines. Friday morning, the wedding party had an early wake-up call for a hot-air-balloon ride together. “It was such a fun morning with our bridesmaids, groomsmen, and significant others to show our thanks for being a part of our wedding weekend,” says Meg. Later that day, there was a pool party at Castello di Casole for everyone as more guests continued to arrive. That night, Michael’s family hosted the rehearsal dinner in the piazza of Casole d’Elsa. “I loved the juxtaposition of the tiny authentic medieval town square Friday night with the grand reception at Castello di Casole on Saturday night and wanted our guests to experience both. We brought in rented tables and chairs to create a dinner setting and strung lights above the town square for a magical ambiance.” Caffe Casolani, a favorite restaurant in town, prepared traditional Tuscan dishes for the event that were served family style. "Casole d’Elsa isn’t a typical tourist destination so the local residents were all very curious as to what was going on in town, and had gathered to observe,” says Meg. “Even the mayor came by to check out the big event! After a little too much house wine, the party turned into dancing in the streets until 1:00 a.m.!”

Next, it was on to the main event: The couple got married at Santa Maria Assunta, a 850-year-old church in the town of Casole d’Elsa, and the traditional Catholic ceremony was officiated by Meg and Michael’s priest from high school. “He had seen us grow up over the last 10 years and knows us both as individuals as well as a couple, so it was very special to have him there,” says Meg. The bride walked down the aisle with both of her parents to the “Prince of Denmark’s March” by Clarke. “My parents are divorced so I decided to have both of them walk down the aisle to recognize them both for helping mold me into the woman I am today,” says Meg.

Florist Vincenzo Dascanio completely transformed the church. “When I first entered, I was stunned,” says Meg. “It was bursting with flowers and candles lining the aisle. I remember looking over my shoulder during communion and seeing tons of locals gathered in the back of the church. I couldn’t believe they were listening to an hour-long ceremony in English!”

The bride wore a dress that she found at the Carolina Herrera boutique on Madison Avenue. “As soon as I put it on, I knew it was the one,” she remembers. “I loved the delicate Italian lace, and it felt perfectly Old World for Tuscany, yet it was also modern and youthful.” She chose a cathedral-length veil with the same lace trim and further accessorized the look with Manolo Blahnik satin pumps and a personalized Edie Parker clutch with her new initials monogrammed on it. She kept her jewelry simple, wearing only her mother’s Graff diamond earrings, her engagement ring—which once belonged to her grandmother—and her Cartier love bracelet. “My grandmother and I were extremely close,” says Meg. “She unfortunately could not attend the wedding due to her poor health, and it being too far to travel. The hardest part about having a destination wedding was not having her there. Wearing her ring that weekend—and every day—makes me feel like I always have a part of her with me. I also kept her lace handkerchief with me all night—my something old.”

After the ceremony, the evening kicked off with cocktails on the terrace of Castello di Casole, where guests had appetizers and drinks under the Tuscan sun. Guests then moved into a tent for dinner. “When you ask 160 of your nearest and dearest to come to Italy, you know you have to blow them away with amazing Italian dishes, so food was a priority all weekend long,” says Meg. In true Italian fashion, they served a five-course dinner, including a seafood salad; ravioli stuffed with ricotta, spinach, and local black truffle; saffron risotto with prawns; sea bass; and roasted veal medallions.

Italian crooner Matteo Brancaleoni—whom the bride found on Youtube!—and his band played throughout the meal. “My wedding planner had never heard of him, so we were taking a pretty big risk,” admits Meg. But, he was absolutely incredible and set the tone for the entire evening. It felt like we were listening to a concert during dinner, and there ended up being much more dancing during the meal than I anticipated!” After everyone finished eating, the rest of the night was spent on the dance floor. “This was exactly where I wanted to be,” says the bride. “Once you’ve said ‘I do,’ the rest of the evening flies by! Before I knew it, the band was playing their last song.” At the end of the party, guests were invited to the terrace for the cake cutting, where a traditional millefoglie, was served. “I had planned fireworks as a surprise for Michael, which went off as soon as we cut the cake,” says Meg. “They started to the Star Wars theme song—his favorite movie—so he instantly knew it was a gift from his bride and couldn’t stop laughing!”